In the world of video games, Jim could be counted on to enjoy two things: the latest Dark Souls and the latest Warriors.
Sekiro has changed Souls enough so Jim no longer enjoys it and wants an easy mode and Warriors has been ruined unless a third party comes in to roll back KT's changes for a reskin and he's too old to find something new he enjoys. Placing these on the timeline of degeneracy, these might be the catalysts for Jim trying to solve all his problems through pretending to be a woman via Little Britain